Simple synthesis of beta-D-glycopyranosides using beta-glycosidase from almonds

Chem Pharm Bull (Tokyo). 2004 Feb;52(2):270-5. doi: 10.1248/cpb.52.270.

Abstract

Enzymatic glycosidation of twenty-one kinds of alcohols (n-hepanol, n-octanol, 2-phenylethanol, 3-phenylpropanol, 4-phenylbutanol, 5-phenylpentanol, 6-phenylhexanol, furfury alcohol, 2-pyridinemethanol, isobutanol, isopentanol, p-methoxycinnamylalcohol) including secondary alcohols (isopropanol, cyclohexanol, 1-phenylethanol) and 1,omega-alkanediols (1,5-pentanediol, 1,6-hexanediol, 1,7-heptanediol, 1,8-octanediol, 1,9-nonanediol), salicyl alcohol and 4-nitrophenyl beta-D-glucopyranoside (5) using beta-glucosidase from almonds stereoselectively gave the corresponding beta-D-glucopyranosides in moderate yield.

MeSH terms

  • Alcohols / chemistry
  • Glucosides / chemical synthesis*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitrophenols / chemistry
  • Prunus / chemistry*
  • Stereoisomerism
  • beta-Glucosidase / chemistry*
  • beta-Glucosidase / isolation & purification

Substances

  • Alcohols
  • Glucosides
  • Nitrophenols
  • 4-nitrophenyl
  • beta-Glucosidase